CN117137822B - Anti-aging composition and application thereof - Google Patents
Anti-aging composition and application thereof Download PDFInfo
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- CN117137822B CN117137822B CN202311427953.1A CN202311427953A CN117137822B CN 117137822 B CN117137822 B CN 117137822B CN 202311427953 A CN202311427953 A CN 202311427953A CN 117137822 B CN117137822 B CN 117137822B
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- wrinkle
- aging
- hexapeptide
- aging composition
- sodium hyaluronate
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/592—Mixtures of compounds complementing their respective functions
- A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18
Abstract
The invention discloses an anti-aging composition and application thereof, and belongs to the technical field of cosmetic peptides. An anti-aging composition comprising: cosmetic peptides and actives; the cosmetic peptide is at least 2 selected from melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 and anti-wrinkle hexapeptide, wherein the anti-wrinkle hexapeptide is Ac-Trp-Phe (4-Cl) -Arg-D-Leu-Ala-His-NH 2 The method comprises the steps of carrying out a first treatment on the surface of the The active substance is at least 1 selected from sodium hyaluronate, sodium hyaluronate amide, ergothioneine and gamma-aminobutyric acid. The components of the anti-aging composition can play a synergistic effect, the anti-aging effect is achieved by improving the expression of the basal collagen, and the anti-aging composition has an excellent moisturizing effect on skin, so that the composition has a strong anti-aging effect due to the anti-aging and moisturizing effects.
Description
Technical Field
The invention belongs to the technical field of cosmetic peptides, and particularly relates to an anti-aging composition and application thereof.
Background
Skin aging is a phenomenon of skin aging caused by natural or unnatural factors. The skin tissue of the human after birth is developed increasingly, and the functions are active gradually. The growth period of skin tissue generally ends around 25 years, and the skin elastic fiber gradually thickens and ages in 40-50 years, so that the aging of skin is obvious. Aging of skin is a natural law, aging resistance is a persistent beauty topic, and although natural aging of skin cannot be prevented, the aging state of skin can be changed through scientific and effective measures. In the cosmetic field, cosmetic peptides have become an important class of active ingredients in the anti-aging field. In the prior art, the invention patent with application number 2017103647182 discloses an anti-aging active compound composition which comprises the following components in percentage by mass: 0.1 to 5 percent of macromolecular sodium hyaluronate; 0.1 to 5 percent of small molecule sodium hyaluronate; human epidermal growth factor 0.1-2%; 0.01 to 0.1 percent of acetylhexapeptide-8; 0.1 to 2 percent of carnosine; water makes up 100%; the active compound has obvious anti-aging function, when being used for preparing cosmetics, the dosage is 1-10% w/w, and the active compound can achieve very obvious anti-aging effect after being used for 30 days, and the skin becomes compact and full and recovers the youthful state. In the prior art, the invention patent with the application number of 2020108182022 discloses an anti-aging peptide composition which consists of tetrapeptides, hexapeptide-11, copper tripeptides, pentapeptides-18 and soybean polypeptides; the mass ratio of the tetrapeptide, the copper tripeptide, the pentapeptide-18, the soybean polypeptide and the hexapeptide-11 is as follows: (5-5.5): (3.2-4): (6.8-8.3): (9.3-10): (0-0.3). The components in the peptide composition are cooperatively matched in a proper mass ratio, so that the peptide composition can be applied to skin, can effectively repair skin injury, has good whitening and anti-wrinkle effects, can not cause secondary injury to skin, and has remarkable anti-aging effects compared with other ratios.
Disclosure of Invention
The invention aims to provide an anti-aging composition with anti-wrinkle and moisturizing effects.
The technical scheme adopted by the invention for achieving the purpose is as follows:
an anti-aging composition comprising:
-a cosmetic peptide selected from at least 2 of melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 and an anti-wrinkle hexapeptide Ac-Trp-Phe (4-Cl) -Arg-D-Leu-Ala-His-NH 2 The method comprises the steps of carrying out a first treatment on the surface of the And, a step of, in the first embodiment,
-an active substance selected from at least 1 of sodium hyaluronate, sodium aminated hyaluronate, ergothioneine, and gamma-aminobutyric acid.
The melittin has antiinflammatory, antibacterial, radioprotective, botulinum toxin-like wrinkle removing, skin collagen and elastin production promoting effects; palmitoyl dipeptide-7 avoids limitation of amino acid ion property by introducing palmitoyl groups, activates an NRF2 signal path to resist oxidation, promotes regeneration of extracellular ECM matrix, restores the compact elastic young state of skin, and resists aging problem caused by matrix loss; the acetyl tetrapeptide-2 has a certain promotion effect on the collagen COL17A1 formed by the DEJ semi-bridged particle, can effectively promote the collagen level and elastic fiber, promote the combination of cells and ECM, and resist adverse effects of skin compactness and adhesion loss; the anti-wrinkle hexapeptide has excellent anti-wrinkle performance and moisturizing performance, has excellent cell survival rate, is safe and nontoxic, and can be widely applied to the fields of skin care products or cosmetics and the like. The sodium hyaluronate is low molecular sodium hyaluronate with molecular weight of 30-50kDa, and has effects of deeply moisturizing skin, improving skin elasticity, and reducing wrinkles; the amino sodium hyaluronate is obtained by coupling amino on gamma-aminobutyric acid to a sodium hyaluronate molecular chain through amidation reaction, and has excellent anti-wrinkle performance and moisturizing performance; ergothioneine can protect DNA and mitochondria of skin cells, resist oxidation and photoaging, reduce color spots and fine lines, and improve skin moisture content and elasticity; gamma-aminobutyric acid is a natural anti-aging factor, and is used for stretching wrinkles, smoothing skin, promoting cell regeneration and repairing damaged skin. The components of the anti-aging composition can play a synergistic effect, the anti-aging effect is achieved by improving the expression of the basal collagen, and the anti-aging composition has an excellent moisturizing effect on skin, so that the composition has a strong anti-aging effect due to the anti-aging and moisturizing effects.
In one embodiment, the cosmetic peptide comprises melittin and palmitoyl dipeptide-7, the active substance is selected from at least 1 of sodium hyaluronate, sodium hyaluronate amide, ergothioneine, and gamma-aminobutyric acid, and the mass ratio of melittin, palmitoyl dipeptide-7, and active substance is 0.5-1.5:0.5-1.5:0.5.
In one embodiment, the cosmetic peptides comprise melittin and palmitoyl dipeptide-7, the active substances are sodium hyaluronate and gamma-aminobutyric acid, and the mass ratio of melittin, palmitoyl dipeptide-7, sodium hyaluronate and gamma-aminobutyric acid is 0.5-1.5:0.5-1.5:0.5-1.5.
In one embodiment, the cosmetic peptide comprises melittin, palmitoyl dipeptide-7 and acetyl tetrapeptide-2, the active substance is selected from at least 1 of sodium hyaluronate, ergothioneine and gamma-aminobutyric acid, and the mass ratio of melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 and active substance is 0.5-1.5:0.5-1.5:0.5-1.5:0.5-1.5.
In one embodiment, the cosmetic peptides comprise melittin, palmitoyl dipeptide-7 and acetyl tetrapeptide-2, the active substances are sodium hyaluronate and gamma-aminobutyric acid, and the mass ratio of melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2, sodium hyaluronate and gamma-aminobutyric acid is 0.5-1.5:0.5-1.5:0.5-1.5:0.5-1.5.
In one embodiment, the cosmetic peptides comprise melittin, palmitoyl dipeptide-7 and acetyl tetrapeptide-2, the active substances comprise sodium hyaluronate, ergothioneine and gamma-aminobutyric acid, and the mass ratio of melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2, sodium hyaluronate, ergothioneine and gamma-aminobutyric acid is 0.5-1.5:0.5-1.5:0.5-1.5:0.5-1.5:0.5-1.5:0.5-1.5.
In one embodiment, the cosmetic peptide comprises acetyl tetrapeptide-2 and anti-wrinkle hexapeptide, and the mass ratio of acetyl tetrapeptide-2 to anti-wrinkle hexapeptide is 0.5-1.5:0.5-1.5. When the acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide are used in combination, the synergistic effect can be exerted, the expression of the related genes of the skin elastin can be obviously regulated, the skin elasticity is improved, the anti-wrinkle and moisturizing effects are achieved, and the anti-aging purpose is realized.
In one embodiment, the cosmetic peptide comprises acetyl tetrapeptide-2 and anti-wrinkle hexapeptide, the active substance is selected from at least 1 of sodium hyaluronate, sodium hyaluronate amide, ergothioneine and gamma-aminobutyric acid, and the mass ratio of acetyl tetrapeptide-2, anti-wrinkle hexapeptide and active substance is 0.5-1.5:0.5-1.5.
In one embodiment, the cosmetic peptide comprises acetyl tetrapeptide-2 and anti-wrinkle hexapeptide, the active substances are sodium hyaluronate and gamma-aminobutyric acid, and the mass ratio of the acetyl tetrapeptide-2, the anti-wrinkle hexapeptide, the sodium hyaluronate and the gamma-aminobutyric acid is 0.5-1.5:0.5-1.5:0.5-1.5:0.5.
In one embodiment, the amino group of the amino sodium hyaluronate is gamma aminobutyric acid coupled to a molecular chain of sodium hyaluronate. The amino sodium hyaluronate is obtained by coupling amino groups on gamma-aminobutyric acid to a sodium hyaluronate molecular chain through amidation reaction, and has excellent anti-wrinkle performance and moisturizing performance.
In one embodiment, the anti-aging composition comprises acetyl tetrapeptide-2, anti-wrinkle hexapeptide, and sodium amino hyaluronate in a mass ratio of 0.5-1.5:0.5-1.5.
In one embodiment, the anti-wrinkle hexapeptide is an anti-wrinkle hexapeptide quaternary ammonium salt.
In one embodiment, the anti-wrinkle hexapeptide quaternary ammonium salt is prepared by reacting anti-wrinkle hexapeptide with carnosine. Compared with anti-wrinkle hexapeptide, the anti-wrinkle hexapeptide quaternary ammonium salt not only has better anti-wrinkle performance, moisturizing performance and biocompatibility. Therefore, the anti-wrinkle hexapeptide quaternary ammonium salt has more excellent anti-aging effect on skin, and has good application prospect as an active ingredient of the anti-aging composition.
In one embodiment, the cosmetic peptide comprises acetyl tetrapeptide-2 and anti-wrinkle hexapeptide quaternary ammonium salt, and the mass ratio of the acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide quaternary ammonium salt is 0.5-1.5:0.5-1.5. When the acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide quaternary ammonium salt are used in combination, a synergistic gain effect can be exerted, the expression of genes related to skin elastin can be obviously regulated, the elasticity of skin is improved, the anti-wrinkle and moisturizing effects are achieved, and the anti-aging purpose is realized.
In one embodiment, the cosmetic peptide comprises acetyl tetrapeptide-2 and anti-wrinkle hexapeptide quaternary ammonium salt, the active substance is selected from at least 1 of sodium hyaluronate, sodium hyaluronate amide, ergothioneine and gamma-aminobutyric acid, and the mass ratio of acetyl tetrapeptide-2, anti-wrinkle hexapeptide quaternary ammonium salt and active substance is 0.5-1.5:0.5-1.5.
In one embodiment, the cosmetic peptide comprises acetyl tetrapeptide-2 and anti-wrinkle hexapeptide quaternary ammonium salt, the active substances are sodium hyaluronate and gamma-aminobutyric acid, and the mass ratio of the acetyl tetrapeptide-2 to the anti-wrinkle hexapeptide quaternary ammonium salt to the sodium hyaluronate to the gamma-aminobutyric acid is 0.5-1.5:0.5-1.5:0.5-1.5.
In one embodiment, the mass of each component in the anti-aging composition is the same.
The anti-aging composition is prepared in the form of an aqueous formulation, and in one embodiment, the anti-aging composition further comprises water. The content of each component in the anti-aging composition is 0.01-1.0wt%.
In a preferred embodiment, the anti-aging composition further comprises a preservative which is p-hydroxyacetophenone and 1,2 hexanediol.
In a preferred embodiment, the content of each component in the anti-aging composition is 0.01 to 1.0wt%.
The invention also discloses a preparation method of the anti-aging composition, which comprises the steps of uniformly mixing the beauty peptide and the active substance, then adding the mixture into water, and uniformly stirring to obtain the anti-aging composition.
The invention also discloses a preparation method of the aminated sodium hyaluronate, which comprises the following steps:
and (3) reacting sodium hyaluronate with gamma-aminobutyric acid in the presence of EDC and NHS to obtain the amino sodium hyaluronate.
In one embodiment, the mass ratio of sodium hyaluronate to gamma aminobutyric acid is 1:1-5.
In one embodiment, the sodium hyaluronate, EDC and NHS are used in a ratio of 1g:3-6mmol:5-10mmol.
In one embodiment, a method for preparing an aminated sodium hyaluronate, comprising:
dissolving sodium hyaluronate in deionized water, adding EDC and NHS, stirring uniformly, regulating pH to 4.0-5.0 by using 0.01-0.1M hydrochloric acid solution and/or 0.01-0.1M sodium hydroxide solution, reacting for 1-3h at room temperature, adding gamma-aminobutyric acid after the reaction is finished, stirring uniformly, regulating pH to 4.0-5.0 by using 0.01-0.1M hydrochloric acid solution and/or 0.01-0.1M sodium hydroxide solution, continuing to react for 12-36h at room temperature, loading the reaction solution into a dialysis bag after the reaction is finished, dialyzing for 6-12h by using 0.05-0.2M sodium carbonate solution, dialyzing for 48-72h by using deionized water, and freeze-drying the dialysis solution to obtain the amino sodium hyaluronate.
In a preferred embodiment, the ratio of sodium hyaluronate to deionized water is 1g:100-200mL.
The invention also discloses a preparation method of the anti-wrinkle hexapeptide quaternary ammonium salt, which comprises the following steps:
adding anti-wrinkle hexapeptide into dimethylformamide, stirring uniformly, adding carnosine, stirring at 70-90 ℃ for reaction for 6-12h, filtering the reaction product, washing 2-5 times by using methanol and dichloromethane respectively, and drying to obtain the anti-wrinkle hexapeptide quaternary ammonium salt.
In one embodiment, the anti-wrinkle hexapeptide and dimethylformamide are used in a ratio of 1g to 10-50mL.
In one embodiment, the molar ratio of anti-wrinkle hexapeptide to carnosine is 1:0.9-1.1.
The invention also discloses application of the anti-aging composition in preparing skin care products.
In one embodiment, the use of an anti-aging composition in the preparation of an anti-aging skin care product.
The invention also discloses a skin care product comprising the anti-aging composition.
The invention also discloses application of the acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide in the preparation of the anti-aging composition, wherein the anti-wrinkle hexapeptide is Ac-Trp-Phe (4-Cl) -Arg-D-Leu-Ala-His-NH 2 。
In one embodiment, the mass ratio of acetyl tetrapeptide-2 to anti-wrinkle hexapeptide is 0.5-1.5:0.5-1.5.
The invention also discloses application of the acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide quaternary ammonium salt in preparing an anti-aging composition, wherein the anti-wrinkle hexapeptide quaternary ammonium salt is prepared by reacting anti-wrinkle hexapeptide and carnosine, and the anti-wrinkle hexapeptide is Ac-Trp-Phe (4-Cl) -Arg-D-Leu-Ala-His-NH 2 。
In one embodiment, the mass ratio of acetyl tetrapeptide-2 to anti-wrinkle hexapeptide quaternary ammonium salt is 0.5-1.5:0.5-1.5.
The anti-aging composition of the invention has the following beneficial effects due to the adoption of the cosmetic peptide and the active substance: the components for the anti-aging composition can play a synergistic effect, the anti-aging effect is played by improving the expression of the basal collagen, and meanwhile, the anti-aging composition also has an excellent moisturizing effect on skin, so that the anti-aging composition has a stronger anti-aging effect due to the anti-aging and moisturizing effects; the combined use of the acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide in the anti-aging composition can play a role in synergistic gain, can obviously up-regulate the expression of related genes of skin elastin, improve the elasticity of skin, achieve the anti-wrinkle effect and realize the anti-aging purpose; the amino sodium hyaluronate used for the anti-aging composition has excellent anti-wrinkle performance and moisturizing performance; the anti-wrinkle hexapeptide quaternary ammonium salt for the anti-aging composition has better anti-wrinkle performance, moisturizing performance and biocompatibility. Accordingly, it is an object of the present invention to provide an anti-aging composition having anti-wrinkle and moisturizing effects.
Drawings
FIG. 1 is a mass spectrum of an anti-wrinkle hexapeptide quaternary ammonium salt;
fig. 2 is a graph showing the moisture retention of aminated sodium hyaluronate and sodium hyaluronate at a relative humidity rh=81%;
fig. 3 is a graph showing the moisture retention of aminated sodium hyaluronate and sodium hyaluronate at a relative humidity rh=0%;
fig. 4 is a graph showing the improvement rate of wrinkles by the anti-aging composition.
Detailed Description
The present invention will be further described in detail with reference to specific embodiments in order to make the objects, technical solutions and advantages of the present invention more apparent.
The experimental methods in the following examples are conventional methods unless otherwise specified. Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
The sodium hyaluronate used in the embodiment of the invention is low molecular sodium hyaluronate, and the molecular weight of the sodium hyaluronate is 30kDa.
The examples of the present invention use anti-wrinkle hexapeptide (Ac-Trp-Phe (4-Cl) -Arg-D-Leu-Ala-His-NH) 2 ) Anti-wrinkle hexapeptide compound 6 in the existing patent (application number 202310826252.9) of Hangzhou surge peptide biochemical technology Co., ltd. With reference to the patent for preparation method and detection test method, the structural formula of anti-wrinkle hexapeptide used in the embodiment of the invention is as follows:
。
example 1:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7 and sodium hyaluronate in a mass ratio of 1:1:1.
Example 2:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7 and ergothioneine in a mass ratio of 1:1:1.
Example 3:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7 and gamma-aminobutyric acid in a mass ratio of 1:1:1.
Example 4:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7 and sodium aminated hyaluronate in a mass ratio of 1:1:1.
The preparation method of the aminated sodium hyaluronate comprises the following steps:
dissolving sodium hyaluronate in deionized water, adding EDC and NHS, and adding sodium hyaluronate, EDC and N at a dosage ratio of 1g:150mLThe method comprises the steps of (1) adjusting the pH to 4.5 by using a 0.01M hydrochloric acid solution and a 0.01M sodium hydroxide solution after uniformly stirring, reacting for 2 hours at room temperature, adding gamma-aminobutyric acid after the reaction is finished, adjusting the pH to 4.5 by using a 0.01M hydrochloric acid solution and a 0.01M sodium hydroxide solution after uniformly stirring, continuously reacting for 24 hours at room temperature, filling the reaction solution into a dialysis bag after the reaction is finished, dialyzing for 12 hours in a 0.1M sodium carbonate solution, then dialyzing for 48 hours by using deionized water, changing water every 6 hours, and freeze-drying the dialysis solution after the dialysis is finished to obtain the amino sodium hyaluronate. Of sodium hyaluronate 1 In the H NMR spectrum, the compounds appeared as-CO-NH-CH at 3.22ppm, 2.30ppm and 1.93ppm 2 -CH 2 -CH 2 CH in-COOH 2 Meaning that gamma aminobutyric acid is linked to sodium hyaluronate to give aminated sodium hyaluronate.
Example 5:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7, sodium hyaluronate and gamma-aminobutyric acid in a mass ratio of 1:1:0.5:0.5.
Example 6:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 and sodium hyaluronate in a mass ratio of 1:1:1:1.
Example 7:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 and ergothioneine in a mass ratio of 1:1:1:1.
Example 8:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 and gamma-aminobutyric acid in a mass ratio of 1:1:1:1.
Example 9:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 and sodium aminated hyaluronate in a mass ratio of 1:1:1:1.
Wherein, the preparation method of the aminated sodium hyaluronate is the same as that of example 4.
Example 10:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2, sodium hyaluronate and gamma-aminobutyric acid in a mass ratio of 1:1:1:0.5:0.5.
Example 11:
an anti-aging composition comprising: melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2, sodium hyaluronate, ergothioneine, and gamma-aminobutyric acid in a mass ratio of 1:1:1:1:1:1.
Example 12:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide and sodium hyaluronate in a mass ratio of 1:1:1.
Example 13:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide and ergothioneine in a mass ratio of 1:1:1.
Example 14:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide and gamma-aminobutyric acid in the mass ratio of 1:1:1.
Example 15:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide and sodium amino hyaluronate in the mass ratio of 1:1:1.
Wherein, the preparation method of the aminated sodium hyaluronate is the same as that of example 4.
Example 16:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide, sodium hyaluronate and gamma-aminobutyric acid in the mass ratio of 1:1:0.5:0.5.
Example 17:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide quaternary ammonium salt and sodium hyaluronate, wherein the mass ratio of the acetyl tetrapeptide-2 to the anti-wrinkle hexapeptide quaternary ammonium salt to the sodium hyaluronate is 1:1:1.
The preparation method of the anti-wrinkle hexapeptide quaternary ammonium salt comprises the following steps:
adding anti-wrinkle hexapeptide into dimethylformamide, wherein the dosage ratio of the anti-wrinkle hexapeptide to the dimethylformamide is 1g to 30mL, adding carnosine after stirring uniformly, stirring and reacting for 10 hours at 80 ℃, filtering reaction products, washing 3 times by using methanol and dichloromethane respectively, and drying to obtain the anti-wrinkle hexapeptide quaternary ammonium salt, wherein the structural formula is as follows:
the method comprises the steps of carrying out a first treatment on the surface of the The theoretical exact value of the molecular weight m/z is 1129.53, M W The theoretical observation m/z was 1130.64 and the mass spectrum was shown in FIG. 1.
Example 18:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide quaternary ammonium salt and ergothioneine, wherein the mass ratio of the acetyl tetrapeptide-2 to the anti-wrinkle hexapeptide quaternary ammonium salt to the ergothioneine is 1:1:1.
Example 19:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide and gamma-aminobutyric acid in the mass ratio of 1:1:1.
Wherein, the preparation method of the anti-wrinkle hexapeptide quaternary ammonium salt is the same as that of example 17.
Example 20:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide and sodium amino hyaluronate in the mass ratio of 1:1:1.
Wherein, the preparation method of the amino sodium hyaluronate is the same as that of example 4, and the preparation method of the anti-wrinkle hexapeptide quaternary ammonium salt is the same as that of example 17.
Example 21:
an anti-aging composition comprising: acetyl tetrapeptide-2, anti-wrinkle hexapeptide, sodium hyaluronate and gamma-aminobutyric acid in the mass ratio of 1:1:0.5:0.5.
Wherein, the preparation method of the anti-wrinkle hexapeptide quaternary ammonium salt is the same as that of example 17.
Test example 1:
performance test of aminated sodium hyaluronate
1. Moisture retention performance test
0.5g of a sample (denoted m) was weighed out 0 ) Placing in a drier with relative humidity RH=81% and allochroic silica gel (RH=0%) respectively, standing at room temperature for 48 hr, and separatingTaking out and weighing at 2h, 4h, 8h, 24h and 48h respectively (marked as m) t ). The moisture retention was calculated according to the following formula: moisture retention = m t /m 0 ×100%。
The moisture retention rates of the sodium amino hyaluronate and sodium hyaluronate under the condition of relative humidity rh=81% are shown in fig. 2, and the moisture retention rates of the sodium amino hyaluronate and sodium hyaluronate under the condition of relative humidity rh=0% are shown in fig. 3, and it can be seen that the moisture retention rates of the sodium amino hyaluronate and sodium hyaluronate under the same humidity condition at the same time point are almost the same, which indicates that the sodium amino hyaluronate and sodium hyaluronate have excellent moisture retention performance as the sodium hyaluronate.
2. Cytotoxicity test
According to 2X 10 5 Seed density of cells/well into 96-well plates, incubator (37 ℃, 5% co) 2 ) After 24 hours of culture, 100. Mu.L of 1.0mg/mL sodium hyaluronate (test group) was added, 100. Mu.L of physiological saline was added to the blank group, and the mixture was placed in an incubator (37 ℃ C., 5% CO) 2 ) Medium in culture wells is discarded for 24 hours, 25 mu L of MTT (5 mg/mL) solution is added into each well for continuous culture for 8 hours, stock solution is sucked, 200 mu L of dimethyl sulfoxide is added into each well, shaking is carried out for 15 minutes for complete dissolution, the absorbance at 560nm wavelength is measured by an enzyme-labeling instrument, and the cell survival rate is calculated according to the following calculation formula: cell viability (%) = mean absorbance of test group/mean absorbance of blank group x 100%.
The cell viability of the aminated sodium hyaluronate was 98.69%, and it can be seen that the aminated sodium hyaluronate has excellent cell compatibility.
Test example 2:
performance test of anti-wrinkle hexapeptide quaternary ammonium salt
1. Cytotoxicity test
According to 2X 10 5 Seed density of cells/well into 96-well plates, incubator (37 ℃, 5% co) 2 ) After 24 hours of culture, 100. Mu.L of 1.5mg/mL aqueous solution of anti-wrinkle hexapeptide quaternary ammonium salt (test group) is added, 100. Mu.L of physiological saline is added to a blank group, and the blank group is placed in an incubator (37 ℃ C., 5% CO) 2 ) Medium in culture wells is discarded for 24 hours, 25 mu L of MTT (5 mg/mL) solution is added into each well for continuous culture for 8 hours, stock solution is sucked, 200 mu L of dimethyl sulfoxide is added into each well, shaking is carried out for 15 minutes for complete dissolution, the absorbance at 560nm wavelength is measured by an enzyme-labeling instrument, and the cell survival rate is calculated according to the following calculation formula: cell viability (%) = mean absorbance of test group/mean absorbance of blank group x 100%.
Table 1 shows the cell viability of the anti-wrinkle hexapeptide quaternary ammonium salt, and it can be seen that the anti-wrinkle hexapeptide quaternary ammonium salt has excellent cell compatibility.
TABLE 1 cell viability of anti-wrinkle hexapeptide quaternary ammonium salts
| Group of | Cell viability/% |
| Crease-resistant hexapeptide quaternary ammonium salt | 99.47 |
| Anti-wrinkle hexapeptide | 100.12 |
2. Anti-wrinkle Performance test
1) Cell inoculation: according to 2X 10 5 Seed Density of the cells/wells were seeded with fibroblasts (lot number Fb19052002, supplied by Guangdong Boxi Biotechnology Co., ltd.) in a 6-well plate, incubator (37 ℃ C., 5% CO) 2 ) Incubating overnight; the formulated samples are shown in table 2.
2) Administration: according to the dosing schedule in Table 2, when the cell plating rate in the 6-well plate reached 40% -60%, the group dosing was performed with a dose of 2mL per well, 3 multiple wells were set per group, and an incubator (37 ℃, 5% CO) 2 ) And incubated for 24h.
3) UVA irradiation: according to the test group, the groups with UVA irradiation were subjected to 30J/cm 2 Is placed in an incubator (37 ℃ C., 5% CO) 2 ) The culture was continued for 24 hours.
4) Collecting cells: after 24h incubation, after collecting the cell supernatant, 1 mL/well PBS was washed twice, 1mL RNAiso Plus was added to each well, and after blowing the lysed cells, the samples were collected.
5) And (3) gene expression detection: RNA was extracted, reverse transcribed to cDNA, and then subjected to fluorescent quantitative PCR detection using 2 -△△CT The method performs result calculation.
Table 2 dosing regimen
The test results of the gene expression of the Collagen I, elastin, MMP-1 and MMP-3 are shown in Table 3, and as can be seen from Table 3, compared with the BC group, the expression of the NC group gene Collagen I is obviously down-regulated, which indicates that the test stimulation condition is effective; compared with NC group, the expression of PC group gene Collagen I is obviously up-regulated, which proves that the positive control test is effective; compared with NC group, test group 1 has an up-regulating effect on the expression of gene Collagen I, which indicates that the anti-wrinkle hexapeptide quaternary ammonium salt can promote the synthesis of extracellular matrix protein and resist the reduction of extracellular matrix protein synthesis caused by UVA irradiation. As can be seen from table 3, compared with BC group, NC group gene Elastin expression is significantly down-regulated, indicating that the test stimulation conditions are effective; compared with NC group, the expression of PC group gene Elastin is obviously up-regulated, which proves that the positive control test is effective; compared with NC group, the test group 1 has obviously up-regulated gene Elastin expression, which shows that the anti-wrinkle hexapeptide quaternary ammonium salt can increase the Elastin content in fibroblasts of skin irradiated by ultraviolet rays, further increase the elasticity of the skin, and has excellent anti-wrinkle effect. As can be seen from table 3, compared with BC group, the NC group genes MMP-1, MMP-3 were significantly up-regulated, indicating that the test stimulation conditions were effective; compared with NC group, the expression of the genes MMP-1 and MMP-3 in PC group is obviously down-regulated, which proves that the positive control test is effective; compared with NC group, the expression of genes MMP-1 and MMP-3 is obviously down-regulated by test group 1, which shows that the anti-wrinkle hexapeptide quaternary ammonium salt can reduce the MMP content in fibroblasts, and has excellent anti-wrinkle effect. From table 3, the effect of the test group 3 on up-regulating the expression of the Collagen I and Elastin genes is better than that of the test group 1, which shows that the combined use of the acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide quaternary ammonium salt can significantly up-regulate the expression of the related genes of the skin Elastin, improve the elasticity of the skin, achieve the anti-wrinkle effect and realize the anti-aging purpose; the up-regulating effect of the test group 4 on the expression of the Collagen I and Elastin genes is superior to that of the test group 2, which shows that the combined use of the acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide can obviously up-regulate the expression of the related genes of the skin Elastin, improve the elasticity of the skin, achieve the anti-wrinkle effect and realize the anti-aging purpose.
TABLE 3 determination of Collagen I, elastin, MMP-1 and MMP-3 Gene expression
The results of the measurement of the expression of the gene of the hyaluronate synthase (HAS 1) are shown in Table 4, and as can be seen from Table 4, the expression of the gene HAS1 of the NC group is obviously down-regulated compared with the BC group, which indicates that the stimulation condition of the test is effective; compared with NC group, the expression of PC group gene HAS1 is obviously up-regulated, which proves that the positive control test is effective; compared with NC group, the expression of gene HAS1 in test group 1 obviously up-regulates Collagen I, which shows that the anti-wrinkle hexapeptide quaternary ammonium salt can obviously increase the content of gene HAS1 in fibroblasts, thereby achieving excellent anti-wrinkle effect.
TABLE 4 determination of HASS 1 Gene expression
| Group of | Amplification factor | Upregulation rate/% |
| BC | 1.00 | / |
| NC | 0.65 | / |
| PC | 2.09 | 222 |
| Test group 1 | 1.35 | 107.7 |
| Test group 2 | 0.93 | 43.08 |
In conclusion, the anti-wrinkle hexapeptide quaternary ammonium salt can up-regulate the expression level of Collagen I, elastin and HAS1 genes and down-regulate the expression level of MMP-1 and MMP-3 genes. Therefore, the anti-wrinkle hexapeptide quaternary ammonium salt can promote the repair of photoaged skin, inhibit the acute photodamage of skin cells, further improve the photoaging of the skin, realize the anti-aging purpose, and has better anti-aging performance than the anti-wrinkle hexapeptide.
Test example 3:
performance test of anti-aging compositions
1. Testing on human skin
30 volunteers aged 40-60 years were selected as test persons to sign written informed consent; the test person was coated on one face with an aqueous solution of the anti-aging compositions of examples 1-21 (the cosmetic peptide and active substance were mixed well, howeverAdding into water, stirring to obtain aqueous solution of antiaging composition with concentration of 2.4wt%, using for 2 times a day, each time in the morning and evening for 28 days, and recording wrinkle depth (D) 0 ) And the depth of wrinkles after 28 days of use (D 28 ) Further, the improvement rate of wrinkles is calculated, and the calculation formula of the improvement rate of wrinkles is as follows: improvement rate (%) = (D 0 -D 28 ）/D 0 ×100%。
The improvement rate of the anti-aging composition on the wrinkles is shown in fig. 4, and it can be seen that the anti-aging compositions of examples 1 to 21 have an improvement effect on the wrinkles after 28 days of use, and the improvement rate is higher than 11%. It can also be seen that the anti-aging composition of example 4 improved the rate of improvement of wrinkles over the anti-aging compositions of example 1, example 3 and example 5, the anti-aging composition of example 9 improved the rate of improvement of wrinkles over the anti-aging compositions of example 6, example 8 and example 10, the anti-aging composition of example 15 improved the rate of improvement of wrinkles over the anti-aging compositions of example 12, example 14 and example 16, and the anti-aging composition of example 20 improved the rate of improvement of wrinkles over the anti-aging compositions of example 17, example 19 and example 21, indicating that the aminated sodium hyaluronate provides better anti-wrinkle effect than the sodium hyaluronate and gamma aminobutyric acid alone or in the anti-aging compositions. It can also be seen that the anti-aging compositions of examples 12-16 all had an improvement rate of 13% over wrinkles, indicating that the combination of acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide quaternary ammonium salt provides a better anti-wrinkle effect. It can also be seen that the anti-aging composition of example 17 improved the rate of wrinkles higher than example 12, the anti-aging composition of example 18 improved the rate of wrinkles higher than example 13, the anti-aging composition of example 19 improved the rate of wrinkles higher than example 14, the anti-aging composition of example 20 improved the rate of wrinkles higher than example 15, and the anti-aging composition of example 21 improved the rate of wrinkles higher than example 16, indicating that the anti-wrinkle effect of the anti-aging composition comprising anti-wrinkle hexapeptide quaternary ammonium salt was better than that of the anti-aging composition comprising anti-wrinkle hexapeptide. It can also be seen that the anti-aging compositions of examples 17-21 all had an improvement rate of 15% over wrinkles, indicating that the combination of acetyl tetrapeptide-2 and the anti-wrinkle hexapeptide quaternary ammonium salt provides a better anti-wrinkle effect.
2. Moisture retention performance test
1. Test requirements
1) Age between 18-60 years (except pregnant or lactating women);
2) The basic value of the forearm test area capacitance skin moisture meter is between 15 and 45 (ComeometerUnit, C.U.);
3) Patients without severe systemic disease, no immunodeficiency or autoimmune disease, the tested parts were not tested for skin treatment, cosmetic and other possible effects on the outcome;
4) Patients with no active allergic disease;
5) The patients with no physical high sensitivity;
6) Hormonal drugs and immunosuppressants have not been used for a month;
7) The test sites are not currently or recently available to other clinical trial participants.
2. Test flow item
a) Screening qualified subjects according to requirements, performing group test, and signing written informed consent;
b) The subject cleaned the inside of the forearm with a dry paper towel and rested in a laboratory at a temperature of (21±1) °c, (50±10)% RH for 30min;
c) The experimenter marks the inner side of the forearm of the subject with test areas, wherein the area of each area is 4cm multiplied by 4cm, the interval is at least 1cm, and the sample areas and the blank areas are randomly distributed in the calibration area on the inner side of the arm, so that the positions of all the sample areas and the blank areas are ensured to be balanced statistically;
d) The experimenter collects the skin stratum corneum moisture content basal value (T) in the inner forearm sample area and the empty area 0 ) Each area was assayed 3 times in parallel;
e) The experimenter uses the test sample in the sample area according to the sample using requirement, and the sample using amount is (2.5+/-0.1) mg/cm 2 Blank areas do not use samples (blank control);
f) Data were collected 4h after using the samples (T 4 ）；
g) Data were collected 8h after using the samples (T 8 ）；
h) The test procedure is ended and leaves the laboratory.
3. Test index
The index names are as follows: moisture content of skin stratum corneum; the test instrument/method is as follows: skin moisture test probe CM825; test area: a forearm marking region; index description: higher values indicate higher skin moisture content.
4. Test sample
Example 12, example 15, example 17 and example 20 anti-aging compositions, the basis value of the moisture content of the skin horny layer (T 0 ) The average value was 30.70 (a.u.).
Table 5 shows the moisture content of the skin stratum corneum of the anti-aging compositions, and it can be seen that the anti-aging compositions of example 12, example 15, example 17 and example 20 all have a better moisturizing effect. It can be seen that example 15 anti-aging composition T 4 Value sum T 8 The values are comparable to those of example 12, example 20 anti-aging composition T 4 Value sum T 8 The values are comparable to example 17, which demonstrates that the aminated sodium hyaluronate imparts a better moisturizing effect to the anti-aging composition. It can also be seen that the anti-aging composition T of example 17 4 Value sum T 8 The values are higher than those of example 12, example 20, anti-aging composition T 4 Value sum T 8 The values are all higher than in example 15, which demonstrates that the anti-wrinkle hexapeptide quaternary ammonium salt provides better moisturizing effect for the anti-aging composition than the anti-wrinkle hexapeptide.
TABLE 5 skin stratum corneum moisture content of anti-aging compositions
| Group of | T 4 /a.u. | Rate of change/% | T 8 /a.u. | Rate of change/% |
| Example 12 | 46.15 | 50.33 | 44.87 | 46.16 |
| Example 15 | 46.83 | 52.54 | 45.79 | 49.15 |
| Example 17 | 48.46 | 57.85 | 47.11 | 53.45 |
| Example 20 | 49.2 | 60.26 | 48.05 | 56.51 |
Conventional operations in the operation steps of the present invention are well known to those skilled in the art, and are not described herein.
While the foregoing embodiments have been described in detail in connection with the embodiments of the invention, it should be understood that the foregoing embodiments are merely illustrative of the invention and are not intended to limit the invention, and any modifications, additions, substitutions and the like made without departing from the spirit and scope of the invention.
Claims (6)
1. An anti-aging composition, characterized by: the anti-aging composition comprises:
-a cosmetic peptide selected from at least 2 of melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 and an anti-wrinkle hexapeptide Ac-Trp-Phe (4-Cl) -Arg-D-Leu-Ala-His-NH 2 The structural formula isThe method comprises the steps of carrying out a first treatment on the surface of the And, a step of, in the first embodiment,
-an active substance selected from the group consisting of sodium amino hyaluronate, or, said active substance comprising sodium amino hyaluronate and at least 1 selected from the group consisting of sodium hyaluronate, ergothioneine and gamma-aminobutyric acid; the amino sodium hyaluronate is obtained by coupling amino groups on gamma-aminobutyric acid to a sodium hyaluronate molecular chain through amidation reaction.
2. An anti-aging composition according to claim 1, wherein: the cosmetic peptide comprises melittin and palmitoyl dipeptide-7, the active substance is amino sodium hyaluronate, and the mass ratio of the melittin to the palmitoyl dipeptide-7 to the active substance is 0.5-1.5:0.5-1.5:0.5-1.5.
3. An anti-aging composition according to claim 1, wherein: the cosmetic peptide comprises melittin, palmitoyl dipeptide-7 and acetyl tetrapeptide-2, wherein the active substance is amino sodium hyaluronate, and the mass ratio of the melittin, palmitoyl dipeptide-7, acetyl tetrapeptide-2 to the active substance is 0.5-1.5:0.5-1.5:0.5-1.5:0.5-1.5.
4. An anti-aging composition according to claim 1, wherein: the anti-aging composition comprises acetyl tetrapeptide-2, anti-wrinkle hexapeptide and sodium amino hyaluronate, wherein the mass ratio of the acetyl tetrapeptide-2 to the anti-wrinkle hexapeptide to the sodium amino hyaluronate is 0.5-1.5:0.5-1.5:0.5-1.5.
5. Use of an anti-aging composition according to claim 1 in the preparation of a skin care product.
6. A skin care product, characterized in that: the skin care product comprising the anti-aging composition of claim 1.
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